Dear Miss Lonelyhearts: I met two girls this summer, and although I got to make out with both of them, neither one of them wanted the whole experience — even though I know what I’m doing.


Dear Miss Lonelyhearts: I met two girls this summer, and although I got to make out with both of them, neither one of them wanted the whole experience — even though I know what I’m doing.

I got "initiated" two years ago when I was 16, by a friend of my older sister. She wanted revenge because my sister stole her boyfriend. I didn’t mind getting used. She taught me lots, and she really knew what she was doing. It was great. But then, I was spoiled for girls my age.

So, this summer I worked out and got a tan and went to the beach every weekend in the burning heat with some friends. I thought I talked a good game with the girls we met — but still nothing much happened. I think they thought I didn’t know anything.

One of them said to me: "What are you staring at?" My buddy told me I was trying too hard and that I shouldn’t stare like a hungry dog. But, when I played it cool, I got less attention. I need a better plan, so what do you suggest?

— Wanting to Win, River Heights

Dear Wanting to Win: Thinking of sex as "winning" isn’t a healthy way to approach dating. If the goal is just sex, it’s plenty obvious to most girls, and they’ll dismiss you.

You really need a female friend/buddy who’s your age to teach you how to talk to a girl in a slightly flirtatious friendly way that could end up in a dating situation — and that may lead to something exciting, eventually.

Then there’s "mutual scouting." A platonic female buddy can subtly dig around and report back on who’s interested in you — and you can do the same for her. It works way better than having to start from zero all by yourself.

Some say it takes the fun out of the chase to know if a girl already likes you when you ask her out. But this summer you didn’t do well with "the chase," so this could be a helpful tactic.

Hot tip: Since you definitely want a sexual relationship, younger girls are a bad idea. Once you’ve gotten smoother, you might consider getting involved with girls who are older — by no more than six months to a year.

In all situations, remember — friendship and flirting first, kisses, necking and fooling around come second, then asking for permission to have sex, third, along with talking about and using protection.


Dear Miss Lonelyhearts: I met my birth mother for the first time the other day. She was funny and I liked her, and I had a hundred questions for her. She didn’t seem to want to talk much about the story that led to my birth. I was shocked to find out she just lived across the city.

When we parted, I asked if she might like to meet again and she said she’d "let me know." That hurt. I have her phone number and she hasn’t called me. Should I call her?

— Wanting More, North End

Dear Wanting More: She’s the one who feels guilty, so she’s not as likely to pick up the phone. So, phone her up and offer to take her out for dinner.

Ask her harmless questions over dinner and talk to her about your interests, travels and plans. Then ask questions about she’s into — easy, friendly questions. When things warm up, ask her a few more personal questions, but not too many, so she’ll see you again. Good luck with this, as it’s bound to be a little awkward — but worthwhile.


Please send your questions and comments to or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6.

Miss Lonelyhearts

Miss Lonelyhearts
Advice Columnist

Each year, the Free Press publishes more than 1,000 letters to Miss Lonelyhearts and her responses to the life and relationship questions that come her way.

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